Composition containing dioxabicyclo [3.3.0] octane derivative

Abstract

A food, drink, pharmaceutical, cosmetic composition or food additive comprising a dioxabicyclo[3.3.0]octane derivative represented by the following general formula (I): <IMAGE> (I) wherein R1, R2, R3, R4, R5 and R6 independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, or R1 and R2 and/or R4 and R5 together form a methylene group or an ethylene group, and n, m and l are 0 or 1; and antioxidant.

We claim: 
     
       1. A pharmaceutical composition comprising a dioxabicyclooctane derivative represented by the following general formula (I): ##STR5## wherein R 1 , R 2 , R 3 , R 4 , R 5  and R 6  independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, or R 1  and R 2  and/or R 4  and R 5  together form a methylene group or an ethylene group, and n, m and l are 0 or 1; and an antioxidant, wherein the ratio of dioxabicyclooctane derivative to antioxidant is from about 0.05 to 20. 
     
     
       2. A pharmaceutical composition according to claim 1, wherein the dioxabicyclooctane derivative is sesamin, sesaminol, episesamin, episesaminol, sesamolin, 2-(3,4-methylenedioxyphenyl)-6-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclooctane, 2,6-bis-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclooctane or 2-(3,4-methylenedioxyphenyl)-6-(3-methoxy-4-hydroxyphenoxy)-3,7-dioxabicyclooctane. 
     
     
       3. A pharmaceutical composition according to claim 1, wherein the antioxidant is tocopherol. 
     
     
       4. A pharmaceutical composition according to claim 1, wherein the action of dioxabicyclooctane derivative is lowering cholesterol value. 
     
     
       5. A food additive comprising a dioxabicyclooctane derivative represented by the following general formula (I): ##STR6## wherein R 1 , R 2 , R 3 , R 4 , R 5  and R 6  independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, or R 1  and R 2  and/or R 4  and R 5  together form a methylene group or an ethylene group, and n, m and l are 0 or 1; and an antioxidant, wherein the ratio of dioxabicyclooctane derivative to antioxidant is from about 0.05 to 20. 
     
     
       6. A food additive according to claim 5, wherein the dioxabicyclooctane derivative is sesamin, sesaminol, episesamin, episesaminol, sesamolin, 2-(3,4-methylenedioxyphenyl)-6-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclooctane, 2,6-bis-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclooctane or 2-(3,4-methylenedioxyphenyl)-6-(3-methoxy-4-hydroxyphenoxy)-3,7-dioxabicyclooctane. 
     
     
       7. A food additives according to claim 5, wherein the antioxidant is tocopherol. 
     
     
       8. A food additive according to claim 5, wherein the action of dioxabicyclooctane derivative is lowering cholesterol value. 
     
     
       9. A food or drink to which a dioxabicyclooctane derivative represented by the following general formula (I): ##STR7## wherein R 1 , R 2 , R 3 , R 4 , R 5  and R 6  independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, or R 1  and R 2  and/or R 4  and R 5  together form a methylene group or an ethylene group, and n, m and l are 0 or 1; and an antioxidant have been added, wherein the ratio of dioxabicyclooctane derivative to antioxidant is from about 0.05 to 20. 
     
     
       10. A food or drink according to claim 9, wherein the dioxabicyclooctane derivative is sesamin, sesaminol, episesamin, episesaminol, sesamolin, 2-(3,4-methylenedioxyphenyl)-6-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclooctane, 2,6-bis-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclooctane or 2-(3,4-methylenedioxyphenyl)-6-(3-methoxy-4-hydroxyphenoxy)-3,7-dioxabicyclooctane. 
     
     
       11. A food or drink according to claim 9, wherein the antioxidant is tocopherol. 
     
     
       12. A food or drink exhibiting enhanced actions of dioxabicyclooctane derivative prepared by adding an antioxidant to a food or drink containing dioxabicyclo-octane derivative, wherein the ratio of dioxabicyclo-octane derivative to antioxidant is from about 0.05 to 20, wherein the dioxabicyclooctane derivative is represented by the formula (I): ##STR8## wherein R 1 , R 2 , R 3 , R 4 , R 5  and R 6  independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, or R 1  and R 2  and/or R 4  and R 5  together form a methylene group or an ethylene group, and n, m and l are 0 or 1. 
     
     
       13. A food or drink according to claim 12, wherein the antioxidant is tocopherol. 
     
     
       14. A food or drink according to claim 12, wherein the dioxabicyclooctane derivative is sesamin, sesaminol, episesamin, episesaminol, sesamolin, 2-(3,4-methylenedioxyphenyl)-6-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclooctane, 2,6-bis-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclooctane or 2-(3,4-methylenedioxyphenyl)-6-(3-methoxy-4-hydroxy-phenoxy)-3,7-dioxabicyclooctane. 
     
     
       15. A method for lowering cholesterol value in a mammal comprising adding to a food or drink a dioxabicyclooctane derivative represented by the following general formula (I): ##STR9## wherein R 1 , R 2 , R 3 , R 4 , R 5  and R 6  independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, or R 1  and R 2  and/or R 4  and R 5  together form a methylene group or an ethylene group, and n, m and l are 0 or 1; and an antioxidant, wherein the ratio of dioxabicyclooctane derivative to antioxidant is from about 0.05 to 20, and administering the food or drink to a mammal in an amount effective for lowering the cholesterol value of said mammal. 
     
     
       16. A method according to claim 15, wherein an effective amount is 1 to 100 mg/day of dioxabicyclooctane derivative and antioxidant orally administered to an adult human. 
     
     
       17. A method according to claim 15, wherein an effective amount is 0.1 to 20 mg/day of dioxabicyclooctane derivative and antioxidant parenterally administered to an adult human. 
     
     
       18. A method according to claim 15, wherein the dioxabicyclooctane derivative is sesamin, sesaminol, episesamin, episesaminol, sesamolin, 2-(3,4-methylenedioxyphenyl)-6-(3-methoxy -4-hydroxyphenyl)-3,7-dioxabicyclooctane, 2,6-bis-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclooctane or 2-(3,4-methylenedioxyphenyl)-6-(3-methoxy-4-hydroxy-phenoxy)-3,7-dioxabicyclooctane. 
     
     
       19. A method according to claim 15, wherein the antioxidant is tocopherol. 
     
     
       20. A pharmaceutical composition comprising a sesamin and/or an episesamin and tocopherol so that the ratio of the sesamin and/or episesamin to the tocopherol is from about 0.05 to 20. 
     
     
       21. A method for enhancing in vivo an action of a dioxabicyclooctane derivative represented by the following general formula (I): ##STR10## wherein R 1 , R 2 , R 3 , R 4 , R 5  and R 6  independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, or R 1  and R 2  and/or R 4  and R 5  together form a methylene group or an ethylene group, and n, m and l are 0 or 1; comprising blending the dioxabicyclooctane derivative With an antioxidant, wherein the ratio of dioxabicyclooctane derivative to antioxidant is from about 0.05 to 20; and administering the mixture to a mammal in an amount effective for enhancing in vivo the action of the dioxabicyclooctane derivative in said mammal. 
     
     
       22. A method according to claim 21, wherein the dioxabicyclooctane derivative is sesamin, sesaminol, episesamin, episesaminol, sesamolin, 2-(3,4-methylenedioxyphenyl)-6-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclooctane, 2,6-bis-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclooctane or 2-(3,4-methylenedioxyphenyl)-6-(3-methoxy-4-hydroxyphenoxy)-3,7-dioxabicyclooctane. 
     
     
       23. A method according to claim 21, wherein the antioxidant is tocopherol. 
     
     
       24. A method according to claim 21, wherein 1 to 100 mg/day of the dioxabicyclooctane derivative and antioxidant mixture are orally administered to an adult human. 
     
     
       25. A method according to claim 21, wherein an effective amount is 0.1 to 20 rag/day of dioxabicyclooctane derivative and antioxidant parenterally administered to an adult human. 
     
     
       26. A method according to claim 21, wherein an effective amount is 1 to 100 mg/day of the dioxabicyclooctane derivative and antioxidant mixture orally administered to an adult human. 
     
     
       27. A method according to claim 21, wherein an effective amount is 0.1 to 20 mg/day of dioxabicyclooctane derivative and antioxidant parenterally administered to an adult human. 
     
     
       28. A method according to claim 21, wherein the action of dioxabicyclooctane derivative is lowering cholesterol value.